The paper places youth transitions and vocational education and training (VET) within the global policy context in which economic competiveness is hegemonic. It compares research from the 1970s/80s, which explored young peoples' lived experiences of VET and youth training schemes with contemporary work on similar themes. It argues that there are continuities and discontinuities in the conditions that young people face in their transitions to waged labour. Continuities can be seen in constructions of working class youth, but also by the way in which policy views the economy as characterised by upskilling. This is called into question when set against the existence of significant numbers of low-waged, low-skilled jobs in the English economy. There are also discontinuities that are the result of changes in class and employment structures. As a result, precariousness has become ubiquitous, with this existing in tandem with labour that is surplus to the requirements of capital. The paper reconsiders youth transitions and re-evaluates the notion of serendipity, suggesting these concepts need to be rethought and reworked in current conditions.